N4-(2-methoxy-9-acridinyl)-N1,N1-diethyl-1,4-pentanediamine | 4292-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N4-(2-methoxy-9-acridinyl)-N1,N1-diethyl-1,4-pentanediamine
• 英文别名: N⁴,N⁴-diethyl-N¹-(2-methoxy-acridin-9-yl)-1-methyl-butanediyldiamine；N⁴,N⁴-Diaethyl-N¹-(2-methoxy-acridin-9-yl)-1-methyl-butandiyldiamin；2-Methoxy-9-(4-diethylamino-1-methylbutylamino)-acridin；1-N,1-N-diethyl-4-N-(2-methoxyacridin-9-yl)pentane-1,4-diamine
• CAS: 4292-64-2
• 化学式: C₂₃H₃₁N₃O
• 分子量: 365.519
• InChiKey: PCAVCGOUIHDLJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  534.0±40.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲氧基吖啶-9-胺 生成 N4-(2-methoxy-9-acridinyl)-N1,N1-diethyl-1,4-pentanediamine
  参考文献：
  名称：

  Kuroda, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1944, vol. 64, # 2, p. 69

  摘要：

  DOI：

文献信息

• Synthesis of Monomeric and Dimeric Acridine Compounds as Potential Therapeutics in Alzheimer and Prion Diseases
  作者：René Csuk、Alexander Barthel、Christian Raschke、Ralph Kluge、Dieter Ströhl、Lothar Trieschmann、Gerald Böhm

  DOI：10.1002/ardp.200900065

  日期：2009.12

  spacered dimeric acridine compounds was prepared. Their ability to interrupt the protein association of prion‐ and Alzheimer‐specific proteins and Ab peptides was explored using a fast screening system based on FACS analysis. The bis‐acridines displayed a higher activity than the corresponding monomers. Among these derivatives, best results were obtained with the 2,4‐dimethoxy‐6‐nitro compound 7h for

  从取代的 9-氯吖啶开始，制备了一系列奎纳克林和间隔二聚吖啶化合物。使用基于 FACS 分析的快速筛选系统探索了它们中断朊病毒和阿尔茨海默特异蛋白与 Ab 肽的蛋白质结合的能力。双吖啶比相应的单体表现出更高的活性。在这些衍生物中，Aβ-肽的 2,4-二甲氧基-6-硝基化合物 7h 和 PrP 的 2-甲氧基-6-硝基化合物 7f 获得了最好的结果。
• Inhibition of <i>Trypanosoma cruzi</i> Trypanothione Reductase by Acridines:  Kinetic Studies and Structure−Activity Relationships
  作者：Susanne Bonse、Christiane Santelli-Rouvier、Jacques Barbe、R. Luise Krauth-Siegel

  DOI：10.1021/jm990386s

  日期：1999.12.1

  Series of 9-amino and 9-thioacridines have been synthesized and studied as inhibitors of trypanothione reductase (TR) from Trypanosoma cruzi, the causative agent; of Chagas' disease. The compounds are structural analogues of the acridine drug mepacrine (quinacrine), which is a competitive inhibitor of the parasite enzyme, but not of human glutathione reductase, the closest related host enzyme. The 9-aminoacridines yielded apparent K-i values for competitive inhibition between 5 and 43 mu M. The most effective inhibitors were those with the methoxy and chlorine substituents of mepacrine and NH2 or NHCH(CH3)(CH2)(4)N(Et)(2) at C9. Detailed kinetic analyses revealed that in the case of 9-aminoacridines more than one inhibitor molecule can bind to the enzyme. In contrast, the 9-thioacridine derivatives inhibit TR with mixed-type kinetics. The kinetic data are discussed in light of the three-dimensional structure of the TR-mepacrine complex. The conclusion that structurally very similar acridine compounds can give rise to completely different inhibition patterns renders modelling studies and quantitative structure-activity relationships difficult.
• Tschernzow; Drosdow, Zhurnal Obshchei Khimii, 1939, vol. 9, p. 1435,1439
  作者：Tschernzow、Drosdow

  DOI：——

  日期：——
• Kuroda, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1944, vol. 64, # 1, p. 59,62
  作者：Kuroda

  DOI：——

  日期：——
• NOVEL MODULATORS OF NRF2 AND USES THEREOF
  申请人：Batist Gerald

  公开号：US20130137694A1

  公开（公告）日：2013-05-30

  There is provided modulators of Nrf2 protein which comprises a compound which binds at least one of the BTB domain, IVR domain and Kelch domain of Keap1 protein, activating or inhibiting Nrf2. There is also provided pharmaceutical compositions containing the modulators, as well as uses and method of use of the modulators for the treatment of conditions.